Does the bolded one happen if you have bought the track from iTunes or only if you have imported it some other way?
B
It doesn't matter where the track comes from, sometimes they give you a copy that's not even in the store anymore, instead of the new "Mastered for iTunes" file that's available
I bought a Beatles song from iTunes, attempted to match it with another account, and it gave me a regular file, I imported the same track directly from my CD copy, and still I only get a regular file. I downloaded the same song from the Internet, and it still gives me a regular file. It is not like they do it on purpose, it's because the match algorithm is so weird that on some songs it DOES give you a Mastered for iTunes file, regardless of where the file came from, even if it is illegally downloaded, or from another store, or from a CD. But with some tracks Match just refuses to give you the MFi version.
The only workaround is delete the song, delete the last 2 or 3 seconds, save it, re-add it to the library, match it, and THEN finally it gives you the MFi version. It works 90% of the time. Although I had like 10 or 20 songs that just refuse to cooperate and they always match to an outdated version, usually an old non-MFi one. But that's rare.
The only thing I don't know is why do I have to go through all that process for Match to actually work, why some tracks get matched instantly to the right MFi version and why others don't. But in my experience the source is irrelevant, hell, even some songs that I bought right from the store, that are MFi files, when I try to match them on another account, they give me an outdated version. So... It's just weird. And some others that are low-quality MP3s actually match.